The product $(A)$ of the given reaction is:

  • A
    $1,2,3,4-$tetrahydroquinoline
  • B
    $1,2,3,4-$tetrahydroisoquinoline
  • C
    Indoline
  • D
    $4-$chlorobutylbenzene

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The correct sequence of reactions involved in the following conversion is:

$A$ is a neutral organic compound $(M.F.: C_8H_9ON)$. On treatment with aqueous $Br_2 / HO^{(-)}$, $A$ forms a compound $B$ which is soluble in dilute acid. $B$ on treatment with aqueous $NaNO_2 / HCl$ $(0-5^{\circ}C)$ produces a compound $C$ which on treatment with $CuCN / NaCN$ produces $D$. Hydrolysis of $D$ produces $E$ which is also obtainable from the hydrolysis of $A$. $E$ on treatment with acidified $KMnO_4$ produces $F$. $F$ contains two different types of hydrogen atoms. The structure of $A$ is

Ethylamine can be obtained by the:

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$A$ colourless substance $'A'$ $(C_6H_7N)$ is sparingly soluble in water and gives a water-soluble compound $'B'$ on treating with mineral acid. On reacting with $CHCl_3$ and alcoholic potash,$'A'$ produces an obnoxious smell due to the formation of compound $'C'$. Reaction of $'A'$ with benzenesulphonyl chloride gives compound $'D'$ which is soluble in alkali. With $NaNO_2$ and $HCl$,$'A'$ forms compound $'E'$ which reacts with phenol in an alkaline medium to give an orange dye $'F'$. Identify compounds $'A'$ to $'F'$.

Which of the following compounds can form alcohol with $NaNO_2/HCl$?

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